luxury houses with terrace for sale Chatham, United States

OPEN HOUSE Sunday, May 24 from 12-2 If you are looking for a move-in ready village farmhouse in Hudson Valley's Columbia County, you have found it! This gut-renovated home in charming and desirable Old Chatham is perfect for a weekend or full-time residence. There are 3 bedrooms (2 primary!), 2 ½ retiled, replumbed and rebuilt bathrooms, a huge dressing room with custom built shelves and clothes racks, a wood burning stove, formal dining room, gourmet kitchen and closets everywhere. The new washer and dryer are conveniently located on the 2nd floor. This home features a brand-new Wolf Stove, Bosch refrigerator and dishwasher, quartz kitchen countertops and gorgeous custom solid wood cabinets, farmhouse sink, thermally efficient windows, new wrap around deck and site-specific water filtration system. The hardwood floors have been stripped, sealed and coated throughout the entire house. The entire exterior of house was stripped, sanded and painted in 2025. The roof was repaired / replaced as needed in 2025. The basement features a freshly- poured concrete basement floor, a Beckett furnace installed in 2017, and hot water heater installed 2017. 23 Frog Alley awaits its new owners. Come see it. Call listing agent Richard Byrne at (646) 342-7125 for information and to schedule a showing.

DEEP ACRES - The embodiment of timeless elegance and refined country living in an unparalleled setting. Nestled in the rolling farmland of Columbia County, in New York's Hudson Valley, Deep Acres is a singular estate blending the grace of an English country manor with the tranquility of pastoral landscapes. Spanning 293-acres across six meticulously maintained parcels, the property blends rolling hayfields with formal gardens, offering unobstructed vistas to the Catskill Mountains, dramatic sunsets and a lifestyle rooted in beauty, craftmanship and serenity. A tree lined drive leads to the stately 4,900 SF Greek Revival manor home where classic architecture meets stately elegance. Adjacent sits a heated three-car garage complete with a 1.200 SF second floor office apartment and a spacious parking court. Entering the home, you will experience some of the finest craftmanship, curated lighting and architectural detailing. The entrance foyer, with a grand staircase to the second floor, is flanked by a Mahogany paneled library and a sunlit breakfast room. Further, is the formal salon and dining room which extend onto a deep southern-style covered sitting porch with views of the far-reaching meadows and Catskill range beyond. The chef's kitchen is designed for effortless entertaining while remaining intimate enough for everyday living. Just beyond the kitchen is a service entrance with access to a private one-bedroom apartment above. Upstairs, the primary en-suite is joined by two additional en-suite bedrooms and a richly paneled home office which connects to a third-floor studio with panoramic views. The finished lower level includes a gym, a fully appointed laundry, a second pantry, a cedar lined walk-in closet and the home's mechanical systems. Every floor is serviced by an in-home elevator. Formal gardens and secret gardens are a masterclass in landscape design and laid out to elicit curiosity and showcase the season's full vibrancy of color, while the surrounding hayfields offer a timeless rural counterpoint. Cool off in the pool or dine al fresco at the pool pavilion - an historic barn transformed into an inviting retreat complete with changing room, full bath, kitchenette and garden room. The second floor of this original timber framed structure offers space for one's future vision. Nearby, is the head house garden complex with gardener's office, workroom, garage and glass conservatory, imported from England - all supporting the estate's fenced in perennial/vegetable garden. Further down a gravel lane is a private two-story 2,900 SF guest house/caretaker's cottage renovated into a 3-bedroom, 2-1/2 bath home, perfect for family or on-site management. A few of the property highlights include a 35-zone irrigation system, landscape lighting showcasing the arboretum quality plantings, multiple back-up generators, high speed internet and connectivity and a property security system. Deep Acres is a rare and complete estate, timeless in its design and masterful in its execution. A Hudson Valley treasure, ready to be experienced.

Quitessential 1831 side hall Colonial. Charming home located in the village of Interlaken in the town of Stockbridge, MA. Just minutes to Lenox, downtown Stockbridge, and the Berkshire Botanical Center. Listen to the babbling water from the Larrywaug Brook and visit the nearby town park. Sit on the deck or around the firepit to soak in the atmosphere of privacy and peace. This 3 bedroom, 1.5 bath house has been meticulously updated. These updates include: roof, windows, deck, painting, kitchen, baths, cement clapboard, wood flooring, laundry on main level. Full walkout basement, oil heat, central air, town water, town sewer. Garage is partitioned for a workshop but can easily be converted to a one-car garage again.

2 bed, 2 full bath Berkshire retreat. The bright, airy living room features warm wood floors that lead into a cozy eat-in kitchen. With a heated sunporch and 1st floor full bath, the home offers multiple inviting spaces to relax or entertain. Step outside to a brand new back deck, an ideal setting for summer evenings. 2 bedrooms on the second floor, with a full bath and dreamy tub. Meticulously-maintained home with a new 200-amp electrical service, this turnkey retreat ensures total peace of mind. Expansive back yard with basketball court and shed. Whether you're enjoying the classic rocking-chair porch or exploring nearby trails and boutiques, this sweet sanctuary is a rare find in the heart of Berkshires.

Pride of ownership resonates through this distinctive Georgian-style brick home proudly set atop a hill in this coveted enclave of stately residences. Live on this historic Crofut Street near the esteemed Pittsfield Country Club and Upstreet Cultural District, and just minutes to Lenox to experience the harmonic complexity of Tanglewood. Experience this solid design, rich in traditional detail and character, boasting five bedrooms and two and a half baths, thoughtfully improved over the long term owners' commitment to preservation and restoration. This prominent manor style home may be coupled with the neighboring guest house which features 3 bedrooms and 1 bath plus a first floor in-law bedroom suite and a 2 car garage, if one so chooses to accommodate extended family, friends, or caregivers.

Renovated modern country retreat near Prospect Lake and Catamount Mountain Ski Resort. This stylish home blends contemporary comfort with natural surroundings. The open living and dining room features a wood-burning fireplace, while the eat-in kitchen boasts high-end appliances, stone countertops and laundry. Two bedrooms and two full baths provide comfortable accommodations. The primary suite offers a brand-new full bath and walk-in closet. Glass doors open to a spacious deck overlooking the private backyard and gentle stream--ideal for morning coffee or evening relaxation. Additional highlights include a detached garage, garden shed, efficient heating and central A/C. New roofs on both the house and shed ensure peace of mind. Available fully furnished and equipped for turnkey enjoyment.

Welcome to a newly built modern farmhouse estate set on 11.7 private acres in the heart of Hillsdale. Arriving via a sweeping driveway, rolling lawns unfold into cultivated fields and far-reaching pastoral and mountain views in every direction. Designed for indoor-outdoor living, this 4-bedroom, 4-bath residence blends modern architecture with the warmth and ease of Hudson Valley living. Clean architectural lines are softened by natural materials, soaring vaulted ceilings, and expansive walls of glass that fill the home with changing light throughout the day. At the center of the home, the dramatic great room rises to a 20-foot vaulted ceiling anchored by a wood-burning fireplace clad in earthy, chestnut-toned marble. Large Arcadia custom glass doors open seamlessly to over 540 square feet of covered outdoor living space, creating an effortless connection between indoors and out—ideal for entertaining, quiet mornings, or long sunset evenings overlooking the landscape. The kitchen was designed as both a gathering space and a functional centerpiece, featuring custom walnut cabinetry handcrafted by a Brooklyn cabinetmaker, integrated Fisher & Paykel and Bosch appliances, an oversized monolithic island, and a 48-inch double-oven gas range. A generous butler’s pantry and bar area adds additional prep space, storage, a second dishwasher, prep sink, and microwave drawer—allowing the main kitchen to remain clean, open, and entertaining-ready. The primary suite is a private retreat with vaulted ceilings, a custom dressing room, and a spa-like bath finished in dramatic Calacatta Violetta marble with soaking tub, oversized shower, and fluted glass steel-framed doors. Upstairs, a second primary suite offers a walk-in closet and marble-appointed bath, alongside an additional en-suite bedroom. A versatile fourth bedroom on the main level offers flexibility as a guest suite, office, wellness room, or media space with direct patio access. Thoughtfully engineered for high-performance living, the home features spray foam insulation, high-performance windows, forced-air heating and central air conditioning, on-demand hot water, Lutron lighting controls, remote-access thermostats, generator hookup readiness, and a heated detached 26x26 two-car garage. Just minutes from Catamount Mountain Resort and the Hamlet of Hillsdale, and within easy reach of Great Barrington and Hudson, the property offers a rare combination of architectural refinement, rural privacy, and access to the Hudson Valley and Berkshires’ celebrated farm-to-table dining, local markets, cultural destinations, and year-round recreation. A modern farmhouse of quiet confidence, architectural clarity, and elevated rural living. (listing agent has a financial interest in the property)

Set just moments from downtown Lenox, this charming New England farmhouse blends classic character with thoughtful modern updates. From the moment you arrive, the home's inviting presence and timeless appeal set the tone for what's inside. The recently renovated kitchen serves as the centerpiece of the home, beautifully designed with quartz countertops and all new appliances--perfectly opened to the dining area to create a seamless and functional space for everyday living and entertaining. A cozy living room is adjacent to the dining room. On the other side of the kitchen, a thoughtfully-designed mudroom and bonus space offers the ideal work-from-home office, complete with a half bathroom, laundry, and direct access to the backyard and patio. Upstairs, you'll find three comfortable bedrooms along with a full bathroom, offering a practical and well-balanced layout. Outside, the fully fenced yard provides a private retreat, enhanced by a newly-installed patio--perfect for gatherings or quiet evenings. A standout feature is the custom treehouse, complete with electricity, creating a truly special space for play or creativity. Additional highlights include a one-car detached garage and close proximity to Lenox's vibrant downtown, known for its shops, dining, and cultural attractions. A rare opportunity to own a move-in ready home that effortlessly combines charm, convenience, and modern living in one of the Berkshires' most desirable locations.

This elegant property on a secluded reach of the Green River epitomizes the concept of indoor/outdoor living. The graceful and meticulously maintained 30 acre estate features specimen trees, established gardens, a lilypond, terraces, pastoral views, and wonderful privacy. The custom home, built by one of the region's premiere builders, has been featured in design magazines, garden tours, and has received a Garden Club of America award for its ethos and thoughtful use of building materials. The house was constructed using sustainable and recycled low maintenance building materials designed to last a lifetime. In addition to the light-filled main house, the property includes the gardens, fenced fields, a 2 car garage with potting room and a studio/guest space/office above. This space overlooks the courtyard and a walled garden. The Gunite pool is surrounded by an espaliered apple tree fence and a generous Goshen stone terrace with space to dine and lounge. The large screened pool house includes a half bath, outdoor shower, kitchenette, and massive two chimney fireplace. Further from the house is the barn complex consisting of a 2 bedroom apartment with yard and patio, a separate studio apartment and four garage bays. A hay/storage barn, cutting gardens, and a separate private drive complete this part of the estate. Hidden from the road, the main house is approached by a long drive lined with mature Scarlet Oaks and masses of daffodils in the spring. A courtyard filled with specimen crabapple trees, stone walls and a meandering walkway creates the welcome entry to this one level home. The exterior walls are planted with climbing hydrangea that blur the lines between structure and nature—a common motif throughout the property. The setting is both well designed and peaceful. The grand entry foyer sets the tone for the house. It connects to an enfilade of rooms filled with southern sun that run the length of the house. The south facing rooms have large windows and french doors that welcome both the light and warmth from the sun on a winter's day and open onto exterior terraces in the fair months. All the rooms have extensive garden and pastoral views. On the east side of the entry is the living room with high, coffered ceilings and a fireplace made with grand tour columns. Adjacent to the living room is the primary suite with doors to a private terrace, shower, and lawn. The velvet covered walls create perfect silence, a jewel box of a room. Dual bathrooms and closet areas with a steam shower and a large soaking tub with views complete the suite. West of the entry hall is the large eat-in kitchen with high ceilings, and coveted AGA range. The kitchen's french doors open onto a blue stone patio with the large lily pond, a view of the fields, and cherry trees which shade an outdoor dining space. The kitchen/service area includes a butler's pantry with extensive storage, and a mudroom that leads to the back door and basement. (The basement consists of laundry room, 2 storage areas, cedar closet, wine room, and a huge finished room with box beds, TV and its own internet. The utility room is spacious and contains the furnace, boiler, the controls for the radiant heat and other mechanicals.) Returning upstairs, the far west end of the house, with perfect evening light, has a cozy sitting room. Adjacent to this is the smaller of the two office/library spaces, another library is located between the guest room and the larger office/sitting room. Both library areas have custom floor to ceiling bookshelves. The larger office has french doors that open to a private and romantic courtyard garden with espaliered peach trees and colorful blooms to attract pollinators. Western windows have views of a fenced field and plantings. This room could easily be reconfigured as a family room or another private sitting area. Steps away from the southern facing terrace, perched majestically on a small rise, is the Parthenon-like pool house, a focal point of the outdoor areas. The adjacent heated pool uses copper ionization instead of chlorine. All the pool services are located in a bunker that allows the outdoor areas to stay completely quiet. Meadow Wood was designed for maximum flexibility. There is space for family, visitors, staff, animals, parties large and small, gardening and potting, and farm equipment. Its magic extends into the impeccable gardens and the woods and fields around it. Step into a world of enchantment and be transported to a realm of natural beauty and tranquility. The intimate spaces and thoughtfully curated common areas throughout the property create an environment that is as classic and timeless as it is fun and whimsical. It is truly a home that seamlessly integrates its beautiful interior with the curated natural beauty that surrounds it.

Conveniently located just moments from downtown Pittsfield, this 3-bedroom, 1-bath home offers a straightforward, well-designed layout that works for everyday living. The open kitchen and dining area act as the center of the home, with plenty of space to gather, entertain, or simply move through your day with ease. An enclosed front porch creates a welcoming entry and adds flexible living space. Off the kitchen, a mudroom provides practical functionality and leads directly to the back deck through sliding doors, making the transition to outdoor space feel easy and natural. Upstairs, three bedrooms offer comfortable accommodations with the flexibility to suit a variety of needs, whether for guests, workspace, or additional living. Set in a location that keeps you close to downtown Pittsfield, Berkshire Medical Center, and Pontoosuc Lake, this home offers convenient access to local dining, shopping, and outdoor recreation without sacrificing day-to-day ease.

A mixed use building in the heart of historic Hudson. This c1860 Federal style brick building is a fabulous investment with four beautifully updated apartments. Gut renovated in 2021, the building is completely turn key and has retained much of its historic charm. You’ll find a studio garden apartment in the lower level, a 2BR apartment on street level which could also be used as commercial/retail space, a 2BR apartment on the second floor, and a stunning duplex takes up the top two stories. Off-street parking for three cars in the rear, a fenced in yard planted with lovely perennials and a deck. With minimal maintenance and a healthy cap rate, 358 Warren is an incredible location, a wonderful opportunity for live/work or a pure investment play. Walking distance to Amtrak and in the heart of all that Hudson has to offer.

Set along the shoreline of Pontoosuc Lake, this lakefront home offers beautiful water views from most rooms and an easy connection to one of the Berkshires' most loved recreational lakes. With an eastern exposure, mornings begin with peaceful sunrises over the water, while the large rear deck and private dock create the perfect setting for boating, kayaking, swimming, or simply enjoying life at the lake. Inside, the home blends classic Cape-style charm with a spacious and functional layout. The main level features an open kitchen, dining, and sitting area overlooking the lake, creating a bright and inviting gathering space. A separate living room with fireplace adds warmth and character, while a first-floor bedroom and full bath provide flexibility for guests or single-level living. The second floor includes three additional bedrooms, another full bath, and a generous landing area ideal for a reading nook, office space, or additional lounge area. The heated lower level provides bonus space for recreation, storage, or overflow guests. Additional features include a fenced yard, oversized one-car garage, generator, six wall-mounted A/C units, and convenient access to the nearby town beach at the end of the street. Whether you're searching for a year-round residence or a Berkshire waterfront escape, 15 Sunrise Street offers the rare opportunity to enjoy relaxed lakefront living on Pontoosuc Lake.

Tucked away at the end of a quiet country road, this 3-bed, 2-bath home offers a true Hudson Valley escape--where privacy, light, and landscape come together effortlessly. Set on just under 4 acres, the property feels expansive in a way that surprises you, with land that stretches beyond expectation and a sense of space that's both peaceful and grounding. Inside, a cathedral ceiling and open floor plan create an airy, light-filled interior where sunlight pours in from every angle. The living spaces flow seamlessly to a generous deck, ideal for long afternoons spent beneath a canopy of mature trees. Upstairs, the en-suite bedroom features its own private balcony--an intimate perch for morning coffee or stargazing at night. Modern convenience meets country living with the addition of a Tesla EV charger, while nearby lake access offers easy enjoyment of warm-weather days on the water. Though the setting is serene, it's far from isolated. Located just minutes from Copake Country Club and Copake Lake, and within easy reach of the ever-evolving dining and cultural scenes of Hudson, Hillsdale, and Claverack, the home strikes a rare balance between retreat and accessibility. Catamount Mountain Resort is just 15 minutes away, while both Hudson and Great Barrington are within a short drive--placing you at the crossroads of some of the region's most sought-after destinations. Just 2 hours from NYC and 2.5 from Boston, this is a place to truly get away--without ever feeling too far removed.

Escape to an exceptional post and beam Berkshire retreat nestled on the east side of Jiminy Peak Mountain Resort. Set on 25+ acres for seclusion and privacy-- eat, play, and live in this 4 bedroom, 2.5 bath chalet style home with countless modern updates. Spectrum was recently added for everyday internet and TV streaming, as well as 5 new high-efficiency mini split air conditioning units for those steamy summer nights. New granite countertops and GE Café and Bosch stainless appliances in the recently refurbished kitchen are a true cook's delight. An open living concept, under a soaring 25 foot ceiling, creates great gathering spaces, from the huge sectional to the plentiful island seating, floor to ceiling window dining frames the outdoors inside, while at the same time cheering on the fun and games at the foosball table. Stoke up the new custom ordered woodstove finished with floor to ceiling stone wall and topped with transom windows to heat the entire upper two floors. Bask in the sunlight streaming through the surrounding glass doors and skylights, letting you gaze at the clouds by day and the stars by night, or walk out to the massive wrap around deck and catch the sounds of nature all around. The floorplan flows to a screened-in porch for outdoor dining, or sit in the midst of all the fun on the deck facing to the east for morning sun or the south for afternoon lounging. An open balcony and loft invite you upstairs to catch a movie or game separate from the great room action and crowd, yet lets you stay connected at the same time. The primary suite is sizable and spacious with a full length window seat for a cozy vantage point watching all that nature has to share. Vaulted ceilings, exposed beams, walls of windows, and tongue-and-groove walls envelope you in the warm glow and rich smell of natural pine walls and floors. The lower level living space offers guest or children's quarters on its own, private level with an additional family room, 3 bedrooms, and a full bath. Comfortably sleeping 12 guests in all, there is plenty of room to host a winter gathering for friends and memories of a lifetime. The new electric 80 gallon hot water heater accommodates a full house of hot showers and baths with ease. The cool, wooden frame built-in double bunk beds add to the allure and enchantment of summer camp or a winter ski lodge. Have it all here as you hike nearby at Mount Greylock or get your game on hunting and target shooting at the Pittsfield Sportmens's Club. Nearby Pontoosuc Lake in Lanesborough is a joy for boating and fishing fun, and ski to your heart's content just over the hill at Jiminy Peak, and partake using your Icon ski pass as the newest mountain on their list. The Clark Art Institute, featuring a new wing beginning in 2026, showcases a a renowned collection and it's just minutes up the road. You pass incredible rolling meadows and farmland with some of the most spectacular views in Berkshire County on your way, but first stop at Jake's Java and Lanesborough Local for coffee and the best breakfast wraps around. Welcome to the sweet country life at home in the Berkshires, with a truly wonderful blend of privacy, nature, sport, country, and culture.